Cyclizations of 5-silyl-substituted 4,5-epoxy-1-alkanols

A configuration dependent mode of ring closure

authored by

Gunadi Adiwidjaja, Holger Flörke, Andreas Kirschning, Ernst Schaumann

Abstract

The preparation and proton-induced cyclization of silyl-substituted 4,S-epoxy-l-alkanols is described The regioselectivity of intramolecular attack of the hydroxy group on the epoxy silane moiety is highly dependent on the configuration of the epoxy alcohols employed. Thus 1,4-anti epoxy alcohols exclusively yield tetrahydropyrans whereas the corresponding 1,4-syn derivates furnish a diastereomeric mixture of tetrahydrofurans.

External Organisation(s)

Universität Hamburg
Clausthal University of Technology

Type

Article

Journal

Tetrahedron Letters

Volume

36

Pages

8771-8774

No. of pages

4

ISSN

0040-4039

Publication date

27.11.1995

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Biochemistry, Drug Discovery, Organic Chemistry

Electronic version(s)

https://doi.org/10.1016/0040-4039(95)01915-5 (Access: Unknown)